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Stuck in a Style Rut? Find Inspiration from Mad Men’s Timeless Fashion

There are many fads that we have left behind. Mid-century fashion is timeless, just like an Eames chair. Mad Men was an instant hit, and a Golden Age of TV phenomenon that captured the hearts of both fans and critics. It also set countless fashion trends. It was not long before lowball glasses, shift dresses, and other styles became popular. The show’s cool sense is evident in the fact that many of the looks from the show are still recognizable today, 15 years after its premiere. We all need a little Sterling Cooper swagger, whether you’re a newbie to Madison Avenue or rewatching the show for the third time like I am because that would just be weird. Don’t pour Old Fashioneds in your Zoom meetings. Back then, that was a much more popular idea.

DON DRAPER: The Man of the Hour

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Proper Cloth

Don Draper’s light gray suit is the only thing that can rival Superman’s cape. Lancelot also has armor. This vintage Calvin Klein suit is a perfect match for Mad Men’s Man of Mystery. If you missed the auction item then this is your chance. Proper Cloth’s Allen Grey wool suit is an exact replica of Don’s beloved old suit, thanks to its lightweight material and one-breasted design. Grab one, put it on and tell Lucky Strike that their ideas don’t work. You will look so good that they might just listen.


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Don Draper will do anything to fill out a polo. Season 2 showed us more of Don Draper’s life outside the office. This striking, neutral shirt is Draper casual at his best. J. Crew’s bowery navy tipped captures that same white trim around the collar which makes Don’s look really shine — because menswear is all about the details, just like advertising.


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Don is a man who cannot relax. This flaw was evident in each vacation episode. Even when he carried his ennui in a carry-on bag, he left space for a pair of stylish swim trunks. You can find the same style and flair in OAS swim shorts with purple tie. The swimwear industry has finally caught up to the boardshorts. These trunks have a retro-inspired cut with a shorter hemline. You’ll get bonus points if Don wears the exact same Ray-Ban Olympians IIs.

BETTY DRAPER: Stepford Subverted


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Betty Draper, restless, complex, and rarely satisfied, is a heartbreaker, a character who would have found more agency if she had lived in a time less oppressive. However, her bold sense of style always comes through. This stunning cashmere coat communicates to anyone who looks at it that she is the owner of 51% of the PTA Fund. TQE is a big fan of Cuyana leather products. We’ve added the short wrap wool cashmere coat as well. Cuyana has a wide range of products, just like Mrs. Draper.


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Betty’s Italian Moment is a moment that I have to gasp at every time I watch it. It’s not the dress or hair that is perfect, it’s the earrings. Mejuri’s Organic Pearl Hoops ($75), have the same wow factor. They are made of solid gold, and they move with a dynamic movement. Why fly to the other side of the world when you can have it delivered right to your door?


The Robyn song is about a woman crying in a party gown. The bold prints of Betty are nothing to cry over. Neither is the faithful Eryn polka-dot mini dress by Anthropologie. This look has a modern silhouette and the same retro pattern. It can be worn for events more festive than Draper’s dinner parties.


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Lisa Says Gah

You’re probably thinking: Megan is more popular than Peggy and Joan? Quel scandale! This certified look queen is a reminder that fashions never change. She draws inspiration from French New Wave in her Quebecois heritage, which is evident in the fruit print that she wore on Don and her Hawaii trip. Lisa Says Gah Mini dress is a modern counterpart to your farmers’ market trip.

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Every time my partner invites colleagues over to his house, I “Zou Bisou Bisou” him. Megan turned that song into a verb with her style sing-along, serenading Don and his coworkers in this iconic black dress. No matter if your S.O. Sezane’s dress will have you the talk of the party, whether or not your S.O. Please excuse me as I review the lyrics…

The Silver Fox

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Although I cannot prove it, I am certain that Roger Sterling was the catalyst for men all over the world to embrace gray hairs. Roger Sterling is the most debonair of all the sharp dressers on the show. He brought back the three-piece suits from the grave. Reiss’ hope modern fit collection would make the man on the door of the house proud. The word “waistcoat’ never sounded cooler.

JOAN HARRIS, Queen of the Roost

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Joan Harris is the most stunning redhead since Rita Hayworth. She commands fear and respect in all those who come across her — as she should. Joan’s razor-sharp takedowns and mic drops, particularly when she wears her signature sheath gown, are the highlights of every episode. M.M.LaFleur’s Jillian dress is the perfect way to gain that confidence. M.M. LaFleur is a female-founded company that specializes in women’s workwear. Joan has a similar philosophy: every office corridor can be a catwalk.

PEGGY OLSON: Miss Independent

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Rag & Bone

Peggy Olson, the glass-ceiling breaker you cheer for in Episode One, is my favorite character. Peggy Olson is the brains behind the operation and not the resident look queen of Mad Men, but her defiant walk into McCann-Erickson was a badass moment. Rag & Bone Peyton polo midi dresses have the same spunky shape that calls for a power walk. Cigarette is not included.

STAN RIZZO: Big-City Cowboy

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Alex Mill

Stag Provisions

Stan may not win you over by Season 7, but he can rock some earth tones. Stan may not have won you over until Season 7, but it’s hard to deny that he has a knack for earthy colors. Stan is a sharp contrast to the suit and tie crowd. He represents the changing tide in men’s style, especially as the series moves towards the 1970s. The corduroy jacket, from Alex Mill, would certainly get Rizzo’s seal of approval.

SALLY DRAPER: The Kids are Alright

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Salon de Yohn

Sally Draper is the perfect character to finish our love letter. Sally Draper, a wide-eyed observer of tumultuous world, grows up in front of our eyes. She often feels like the show’s heart. She’ll surprise you like any teenager. Our jaws dropped when we saw little Sally in this Space Age mod mini dress. A fashionista rises!! Salon de Yohn offers the silver spangle mini dress for today’s Sallys. It’s only $181 and will take you to the Moon. Oh, you kids keep me young.

Matthew Weiner said Mad Men is not a novel, but rather a collection short stories. These outfits are short, stylish vignettes that will leave you wanting more. Even though the days of Rolodexes, three-martini meals and Rolodex may be gone, there is always a reason to pick up some 60s-inspired clothing. You’re not alone if you feel the need to rewatch a movie while you are at it.

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